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Construction of Chiral Quaternary Carbon through Morita–Baylis–Hillman Reaction: An Enantioselective Approach to 3‐Substituted 3‐Hydroxyoxindole Derivatives

2010; Wiley; Volume: 16; Issue: 46 Linguagem: Inglês

10.1002/chem.201002240

1521-3765

Xiaoyang Guan, Yin Wei, Min Shi,

Carbohydrate Chemistry and Synthesis

Chemistry – A European JournalVolume 16, Issue 46 p. 13617-13621 Communication Construction of Chiral Quaternary Carbon through Morita–Baylis–Hillman Reaction: An Enantioselective Approach to 3-Substituted 3-Hydroxyoxindole Derivatives Xiao-Yang Guan, Xiao-Yang Guan State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this authorDr. Yin Wei, Corresponding Author Dr. Yin Wei [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this authorProf. Dr. Min Shi, Corresponding Author Prof. Dr. Min Shi [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this author Xiao-Yang Guan, Xiao-Yang Guan State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this authorDr. Yin Wei, Corresponding Author Dr. Yin Wei [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this authorProf. Dr. Min Shi, Corresponding Author Prof. Dr. Min Shi [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China), Fax: (+86)-21-64166128Search for more papers by this author First published: 19 November 2010 https://doi.org/10.1002/chem.201002240Citations: 76Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract A new enantioselective approach to obtain a tetrasubstituted chiral center at the C3 position of oxindoles via a catalytic asymmetric Morita–Baylis–Hillman reaction has been demonstrated. This reaction provides 3-substituted 3-hydroxy-2-oxindoles in good to excellent yields and ee values, which could be facilely transformed to pharmaceutically more interesting compounds. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201002240_sm_miscellaneous_information.pdf1.5 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume16, Issue46December 10, 2010Pages 13617-13621 RelatedInformation